Fluoride-mediated elimination of allyl sulfones: Application to the synthesis of a 2,4-dimethyl-A-ring vitamin D3 analogue

Article abstract of DOI:10.1021/jo300672a

A coupling strategy for the synthesis of 2,4-dimethyl-1α,25(OH) ₂D₃ is achieved which involves methylation of a pro-A ring vinyl sulfone and in situ traping of the allyl sulfonyl anion with a CD ring allyl chloride. TBAF-promoted 1,2-eliminative desulfonylation and concomitant silyl ether deprotection gives the vitamin D₃ analogue.